


Ready For Work

by theotherdesanta



Series: Revelations And New Habits [1]
Category: Grand Theft Auto V
Genre: Drag, Lost Masculinity, M/M, Michael finds out he likes to play dressup, Mike 2 fabulos for u, Swearing, We need more Michael in drag, Well in Mike's case, ladies night
Language: English
Status: Completed
Published: 2016-07-18
Updated: 2016-07-18
Packaged: 2018-07-24 18:57:52
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,392
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7519532
Author URL: https://archiveofourown.org/users/theotherdesanta/pseuds/theotherdesanta
Summary: <blockquote class="userstuff">
              <p>Ladies Night at the Vanilla Unicorn takes an interesting twist when the sweet dame in charge of the register calls in sick and with no time to find a replacement the manager calls in a friend. As with anything Philips adds a small condition to said friends business attire, little does he know it's about to awaken something neither of them knew lurked beneath the surface.</p>
            </blockquote>





	Ready For Work

**Author's Note:**

> I can't really say what inspired this other than bingeing fallout 4 and having my character run around in a dress after painstakingly wasting hours of my life to get him to look as close to Ned Luke as possible. Somehow I wound up somewhere between Ned Luke and Collin Firth. Fucking forward sliders are impossible to use BUT I hope you enjoy this fic as much now as you guys did before. I'm gonna do a big repost today and then save "Closeted Lust" for Friday. No idea why I just think Friday is a good time to post smut. I apologise for spamming you all with my terrible fanfiction. I love you and thanks for all the support. I've really needed the last months and especially now. 
> 
> Piece homies!

“Am I really gonna do this?” A simple thought erupted verbally, bouncing off the expertly decorated mansion walls. Meanwhile, the person whose cracked ever so minutely ajar, thin lips the sentence existed stood mannequin still beyond the reflective glass roughly inspecting the folded pile occupying both hands. “Talk about an exercise in humility” The next escaped in the form of a long defeated sign, as if all hope were lost regarding a brief explanation to why Michael would not be wearing such a getup nor asking if he were allowed to shop for himself, least that way he'd be capable of choosing something a bit less....raunchy. That was the word for it, right? Little too much cleavage on show, tight fabric around the ass, cutting off just below the knee to offer some remnant of modesty. Heh, like Trevor understood modesty, probably didn't know what the fuckin' word even meant. Fighting him on the matter would be a lost cause and further his justification on why Michael's promises remained forever broken or carrying a high price. This was about faith, trust, two things he rarely confided in his running buddy. However, that'd change if he just put on the damn clothes T'd bought and go to the Vanilla Unicorn's advertised 'Ladies Night' to work as Vanessa's replacement at the ticket counter. If Michael got there early and sat himself down behind the bulletproof glass he might've gotten away to a few Martini-soaked glances, if the customers were sober that was, enough to register they were addressing a living person and not a machine pumping paper and inhaling cash like it's motor ran on their sexed up, g-stringed, low cut addictions. Michael craned his neck to get a glimpse of the clock sat atop the polished bedside cabinet: 6:21 PM/Wednesday spelt out in a bold cheap tomato sauce red. Under two hours before he needed to start waddling all that meat down to the tailgater but the ride, depending on traffic and the speed of his driving, would've no doubt taken less than fifteen minutes. Less to worry about, though he was sure fretting over minor setbacks weren't as debilitating as what colour shoes to match with a dark hue skirt which showed off more calve than he'd like. Heaving his body weight across the floor Michael closed in on the bed and placed the five clothing items down on the sheet, slowly spreading them out beside each other to decide what he should attempt to dress in first.   
Removing the fraying jeans he current had belted to his waist felt...oddly cold, dreadful in a sense, the sensation etched a path along his inner thigh, cascading until it reached the ankle where the jeans bunched after having removed the leather strap keeping them aloft. He gingerly stepped out of them and proceeded to tug away the flannel jacket and wife-beater, tossing them away delicately and watching them land against the footboard of the bed. Now standing in a pair of Alvin Aine briefs, he took a deep breath through his nose before slowly pursing his lips and releasing it following a 5-second hold. Michael repeated himself to the point he deemed it unnecessary and time to 'Man up', though huffed a small whimper as his sight collided into the rabbit and cashmere velvet lined undergarments sporting a tag labelling it from the newest piece out of the Magnolia's Shush range. An expensive piece of lingerie designed for the, ahem, fuller figured woman of Los Santos. Michael's dick all but shrivelled as he picked it off the bed using two fingers and made a pale face as he bent double to slip his legs through the holes. Fur on crotch, not something a man should have to experience in his lifetime. Not as bad as he feared but not pleasant either. His turned to the black stockings and skirt, sitting himself down before tackling the lengthy chore of not ripping the thin material as he fought to get them over his feet and scratchy leg hairs, sure they were going to play a role in destroying the stockings. Thanking whatever supreme being laughing at the world below them right then he puffed a relieved sigh and started unbuttoning the left side of the navy blue, waist clenching, mid length skirt. “Oh yeah, this is where things get messy” Michael gritted between clenched teeth, sucking in the ten years of accumulated chub before quickly looping the buttons through their respective slots and falling limp on the mattress, letting his body adjust to the vice-like grip of the skirt and his ego to how ridiculous he would look once dressing was complete. “Do I like Trevor all that much, anyway?” Michael asked himself, wishing for an answer like someone else what to say to him in that moment. “If I didn't...would I even bother going this far?....Probably not” He blinked, rolling to have his eyes fall on the last piece of clothing before he moved on to whatever shoes Trevor had picked out for him, and then make up, hell why not hammer in that last nail, it wasn't like he'd survive the embarrassment and dare tell the tale of their crazy friendship experiment anyways. “Okay, lets hope he...you gotta be kiddin' me here” Michael had forgotten the next item on his list...the bra, no women would be seen outside without something to keep those chest puppies nice and high for the world to see. “Oh no, please, no. Nah-ha-hoooo. Oh god...” He slammed a hand over his face. “I wonder if Doctor Bahone can pencil me in for surgery, I mean why not take the leap and make it official, am I rite?. I mean, pretty much lost every ounce of my masculinity already! WHY NOT BECOME A WOMAN AND JUST GIVE UP DICKHOOD ALL TOGETHER!?” He wiped the hand down his face and closed his eyes, following instructed punched into his phone's web browser on how to put on a bra. Twenty minutes of fidgeting and swearing, Michael didn't dare look at his reflection till the transformation was done. Numbly he threw on the blouse, Eggshell white with frills lining the neck, buttons trailing down too far below the navel and one decorating each folded cuff. Michael went about tucking the messy bits under the skirt, checking to confirm it was neatly hidden away and all you saw was the well fitted, curvaceous form he was displaying. At last...he could move onto the shoes and determine if he was chicken enough to call and cancel his spot at the Unicorn. Michael didn't care what Trevor thought of him, Jesus Michael didn't know what he thought of himself. He felt...to say wrong would be a gross exaggeration, to say shameful was...bordering his emotions but would not stand entirely on point. Michael felt strange, off but...with a new sense of identity filling in the blanks where the name “Townley” disappeared. No longer visible yet still existing behind the “De Santa” facade. He went to the Goch and Dabana box at the end of the room and lifted the list, a pair of smart black kitten heels twinkling in the light thrown by the ceiling chandelier. He gulped, taking one out and bracing a hand on the table as he contorted his upper torso and leg to fit the shoe onto his size 10 foot. Perfect fit, ironically, Michael never imagined to own anything and have it go on as easy as they had. The second shoe was a tad of a squeeze but he put that on the face his foot may have been swollen from that morning's jog with Mary-Anne, The woman could give Usain Bolt a run for his damn money the way she powered around LS. Finally getting into the footwear, Michael shyly tiptoed to the mirror, edging himself piece by piece and then witnessing his own face recede into what looked like a very, very faint smile. The sort you'd expect from a child being in the presence of strangers, unknown family members, even fellow children at a different school or perhaps someone visiting a new place and having to interact with the locals, asking for their help to reach wherever it was they planned on going. It was the nervousness, the raw anxiety threatening to split the seams of the person's well constructed socially acceptable outfit. Something they'd spent a good deal of their lives crafting so no other human being could see through them. Also, it was the unknown. Fabien said it and on that day Michael wanted to hear nothing about it while he smashed the teeth of the guy pulling Michael's wife back into his pelvis. “Do not fear the unknown, we are the unknown” That was the shot. Michael didn't know how his appearance would affect the others, be it friends, random street walkers...his family...Trevor. Michael hated it but being truthful...he was terrified of the unknown. Lack of control, no foresight into what could be a huge shoot out where everyone but him gets out alive. Though he sort of doubted it'd go that far. He swayed a little on one foot, admiring Trevor's eye for fashion and the smooth curves beginning at his pinched waist. Hell, a phone call and Michael could've been on Keeping up with the Cunt-Dashions. He had the ass of one.   
No matter what others said, T really did have an amazing taste, hilariously, for everyone BUT himself. Fact, he was the reason Tracey got into the designer/makeup/celebrity artist/ camera stuff. Always reading magazines to get her to sleep as a kid and letting her stay up to watch Oprah when Mike and Amanda were out of town visiting the parents or moving another shipment of prostitutes. Hipster-ish and grungy as he was, T had a career in fashion, if only the dim fuck had realised that and go made something of his life. “Hey handsome, lookin' for a good time?” Somehow Michael's uneasiness gave way to humorous comedy routines in front of the bedroom mirror, putting one hand on his hip and throwing out what some would call 'gold' and laughing alone to his own jokes. It was comforting as it was a sign he might be going a touch loopy in his old age. Michael snapped his head to look at the clock and hissed when it blared back at him the time announcement: 7:52PM/Wednesday. “CRAP!” Holding the banister as he hurried down the stairs, Michael bolted from the house without dabbing on a lick of concealer which he cursed himself for on the drive toward the Unicorn. “Cmon, let Amanda have put something in here---Glasses. She put my reading glasses in here?....Greaaaaaaatttt” he said, rummaging around the glove compartment. Waiting at the stop lights Michael found a half empty tube of lip gloss his daughter must've left behind during one of their lunches or by Amanda purposely to establish dominance, no idea how she'd do that with a tiny orange tube of cosmetic goop but hey! Michael wasn't about to get into that heap of bullshit anytime soon. Having flipped a finger to the family in the opposite car who stared at him while he donned the gloss and wide, square framed glasses, Michael pushed the gas and rushed through the city before screeching into the Vanilla Unicorn parking lot. He took the nearest space and killed the engine, breathing as he looked at his watch and saw it read 8:05. Not too bad. He doubted anyone had turned up yet besides Trevor's merry band of lusty strippers and other employees. Hastily he trotted to the managers entrance, paying no attention to the group outside sharing a “Before work” smoke as he passed. Thankfully no one was in the room as Michael scuttled in, throwing his coat on the chair and running fat fingers over his greying tufts of what was once thick chocolate brown hair. “Treber!” Wade's voice startled Michael as he finished poking and prodding at his head and slathered on another layer of glitter heavy raspberry scented gloss over his lips. On the desk was a lone, unmarked name tag, it rested atop a clipboard and some coffee stained paperwork. If he wanted to seriously look like what he imagined Trevor coming back to....He'd need to be quick with that pen. “Should I get the girls ready?! Summa-them still ain't got no oil on their skin” Michael's heart jumped when the bellowing reply shook the foundations of the building. “Girls put the oil on their skin OR ELSE WADE GETS THE HOSE AGAIN!” He slapped a hand under his nose as he burst into a snort, finding Trevor's vile response somehow the best thing he'd heard all week. “You know I don'ts like water, T!” Wade's footsteps were audible while he scampered about the dressing room, earning screams from the female dancers who demanded he get out, which he did, and was ordered to go stock the bar fridge and get more ice since Trevor was hinting at a big turnover that night of alcoholic drinks, most with ice. “Be back in a sec, I just need to make a phone call” T's voice rung throughout the narrow hall, even as he began muttering bitterly to himself about Michael's absence. “Where is that slimy weasel? I told him 8 on the dot. No surprise if he cancel on me because he's too afraid of trying a little drag for one evening. Knew this friendship thing was a bad idea, I fuckin' knew it, but NOOO—HOOOOOO—OOOO! I had to put my hopes in Michael and once again he's----” Trevor opened the door, muscles going rock solid as he walked straight in on Michael, standing there holding the clipboard and files, name tag pinned neatly to his blouse. If it wasn't that he was everything T had ever dreamed of when he picked out that combo, the name written down would've done the fucking trick: Mrs M Philips.   
“So you gonna put me to work?” Was all Michael had to say to get the others face to go beet red. That, and the cheesy winners grin that had his dimples showing. 

The end.


End file.
